"The coolest thing that happened to me was that Thomas Mann—as in me—was an answer in TheNew York Times crossword puzzle!" the 24-year-old actor howls with excitement. Mann has long been a household name, but since the newcomer's breakout performance as an awkward high school wallflower in last year's Sundance-winning film Me and Earl and the Dying Girl, its popular reference actually has something to do with him. "Before that, it's always been the 20th-century novelist."

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In the bildungsroman of Thomas Mann, the actor, Me and Earl marks the formative coming-of-age moment. "We kind of decided the roles were ours before our director had," he says of co-star Olivia Cooke, now a close friend. But the match wasn't as obvious to director Alfonso Gomez-Rejon, who called Mann back for seven auditions and came just short of telling him to forget about it before handing him the lead. "Olivia said she felt like she was cheating on me," Mann laughs. "She had to go read with these other guys for the same part."

There's something endearingly juvenile about Mann's bushy-tailed enthusiasm for acting, which (along with his boyish good looks) is perhaps why he's become a go-to for the role of high school underdog heartthrob. Most recently, he starred in the unlikely-yet-true '80s-set flick The Preppie Connection, as a dopey freshman who tries to impress his rich classmates by becoming a drug trafficker. But he's graduated from that character, he says (he himself finished the second half of high school online, moving from Dallas to Los Angeles with a friend's family to pursue acting). Here, Mann tells Bazaar about what happens when your new girlfriend think she's going insane—which is the plot of his next movie, Brain on Fire, co-starring Chloe Moretz—and rollerskating with Brie Larson in Australia while filming Kong: Skull Island.

Harper's BAZAAR: You went to seven separate auditions for Project X and endured a brutal waiting period while waiting to hear back from Me and Earl and the Dying Girl. What goes through your mind when you wait out those long auditioning periods?

Thomas Mann: It's brutal. It's never fun. There were a couple of times that they told me it was not going my way and that I could just forget about it for Project X. Me and Earl was the same way. I did a read with Olivia. Then they casted Olivia, and I had to go in to read with her and two other guys autidioning for the same role.

HB: It sounds like competing on The Bachelorette.

TM: It sort of was! Olivia said she felt like she was cheating on me because she'd already really liked reading with me, and she had to go read with these other guys for the same part.

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HB: You speak very passionately about Me and Earl. Did you view it as a turning point in your career?

TM: Definitely. It's one of those parts that everyone's waiting to fall into their lap—you read something, and it just sounds like your voice, like it's written for you. I'd never felt that way before I read Me and Earl and the Dying Girl. I'd never really been able to show that much of myself in my character. I don't expect to have a part quite as good as that one for a while. They're few and far between.

HB: There was an intense six-minute single-take scene between you and Olivia in that movie that you called your proudest moment. How did you prepare for it?

TM: It helped that Olivia and I really understand not only the characters but also each other. We tell each other everything—like down to when we're going to the bathroom—and never get embarrassed together. We had also done it so many times during auditions that we didn't rehearse it while filming. We wanted to lay it all out there in the first few takes and keep it fresh.

HB: What did you learn about yourself as an actor on that film?

TM: It opened me up emotionally, as an actor and as a human. I grew up a lot on that set, and I think I have more empathy now. You see yourself in a character sometimes, the good and the bad, and it forces you to reflect on your own life. I'm not saying acting should be therapy, but it was definitely a cathartic experience creating something I'm truly proud of that hopefully people will watch for a long time.

HB: When did you and Olivia get so close?

TM: We had dinner a couple of times throughout the audition process and kind of decided the roles were ours before our director [Alfonso Gomez-Rejon] had. From our first audition we knew it felt right. We were already hanging out and discussing the parts, hoping that we'd get them together. Then when we did, and it felt inevitable.

HB: Do you often feel that level of confidence in auditions?

TM: No, no. It was a rare connection. It was a big experience for both of us, as actors and as people, and we went through a lot together. I think we're going to be friends for a long, long time.

HB: Who are some of your other closest acting friends?

TM: My closest acting buddies are the ones I met when I first moved out to LA and didn't know anyone, like my buddy Keir [Gilchrist], who I did It's Kind of a Funny Story with, my first film, back in 2010. My friend Logan [Miller], who I moved out to LA with from Texas, is also an actor and was in Stanford Prison Experiment with me. Recently, I just finished filming Kong: Skull Island and made so many great new friends, like Jason Mitchell, John C. Reilly, and Brie Larsen.

HB: I saw on you roller skating with Brie Larsen on your Instagram. Is that a habitual activity?

TM: Well, we shot Kong in Australia, and Brie would have to go back home to do press for the Oscar stuff most weekends. There was this one weekend when she stayed back and decided, "This is going to be the Brie-kend." We planned all these activities that were Brie-friendly. She loves karaoke and kind of childish activities, so we got the whole Kong crew—a bunch of adults—roller skating like little kids. It was a great time. I got along with that cast so well. We really had a blast.

HB: What was it like returning to high school for The Preppie Connection?

TM: I did that one right on the heels of Me and Earl—in which I also played a guy in high school—with almost no time in between. The movie was set in the '80s, and the pace was really fast. It was a great time. Next, I want to do something a bit darker and more grown up. I definitely can't go back to high school.

HB: Does it annoy you that you're not the first Thomas Mann to appear in a Google search?

TM: Yes! The coolest thing that happened to me was that Thomas Mann—as in me—was an answer in TheNew York Times crossword puzzle! Before that, it's always been the 20th-century novelist.

HB: Take that, Thomas Mann! Have you read any of his work?

TM: I feel like I should. Everyone's always asking me about it, and every once in awhile, someone will be like, "You should read Death in Venice, man. You'll like it."

HB: As a young actor, you must develop a mentor-mentee relationship with older actors in the industry whom you've worked alongside.

TM: Not to put that on anybody and be like, "You're my mentor, now," but I have befriended some more veteran actors. Emma Thompson, who I worked with on Beautiful Creatures, is so wise about the industry and how to find yourself as an artist and not get lost in all the bullshit. And more recently, John C. Reilly has become a great friend of mine. He has good advice and has worked with a lot of great people.

HB: Are there any actors or directors you're dying to work with?

TM: There's obviously the greats, like Scorsese or Thomas Henderson or the Coens. There are some independendent and foreign directors I'm also dying to work with, like Yorgos Lanthimos, who did The Lobster, and Lynne Ramsay. Okay, now I'm just listing things that I like.